Raymond holiday rentals

We found 832 holiday rentals — enter your dates for availability
Select from 89 homes, 54 cottages and other holiday rentals in Raymond to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for spending time at your holiday home, including parking and a TV. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Raymond

Showing deals for:18 Dec - 25 Dec

Interior
Coffee deck off downstairs master bedroom
Exterior
Extra large Living room with plenty of seating
Exceptional
(45 reviews)

Crescent Lake Lakefront gorgeous sunsets, outdoor firepit , big dock, swim float

Raymond

8% off
AU$7,764
for 7 nights, 1 home
AU$1,109 per night
includes taxes & fees
Crescent Lake Lakefront gorgeous sunsets, outdoor firepit , big dock, swim float
View from kitchen table.
View of deck and lake from living room window.
Dining area with view of lake.
Exterior
Exceptional
(39 reviews)

Moose Pond Denmark ME, Lakefront Cottage with Dock, Sleeps 5

Denmark

12% off
AU$2,901
for 7 nights, 1 cottage
AU$414 per night
includes taxes & fees
Moose Pond Denmark ME, Lakefront Cottage with Dock, Sleeps 5
Private kitchen
Living area
Terrace/patio
Dining
Exceptional
(21 reviews)

Luxury Log Cabin • Paradise in the Lakes Region

Naples

8% off
AU$6,495
for 7 nights, 1 home
AU$928 per night
includes taxes & fees
Luxury Log Cabin • Paradise in the Lakes Region
Main floor living room
Patio
Downtown Naples along the Causeway
Interior
Exceptional
(49 reviews)

Luxury English Country Home

Naples

8% off
AU$6,889
for 7 nights, 1 home
AU$984 per night
includes taxes & fees
Luxury English Country Home
View of the river that leads into Sebago Lake.
Library to read a book with a cool breeze from the water!
Brandy Pond has marinas to rent boats.
View from 2nd floor deck
Exceptional
(162 reviews)

Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!

Naples

8% off
AU$1,501
for 7 nights, 1 cottage
AU$214 per night
includes taxes & fees
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Room
Living area
Property grounds
Dining
Exceptional
(11 reviews)

Luxury Lakefront home on Sebago Lake W/ Sandy Beach

Raymond

8% off
AU$7,767
for 7 nights, 1 home
AU$1,110 per night
includes taxes & fees
Luxury Lakefront home on Sebago Lake W/ Sandy Beach
Exterior
Private kitchen
Private sandy beach area
Outdoor dining
Wonderful
(5 reviews)

Lakefront 15 mins from Portland with Private Beach and Fenced in Yard

Windham

20% off
AU$7,133
for 7 nights, 1 home
AU$1,019 per night
includes taxes & fees
Lakefront 15 mins from Portland with Private Beach and Fenced in Yard
Back door porch leads to the firepit and water.
Rent a boat during your stay. Many marinas in the area.
Cool breeze from the river!
Firepit photo taken from the riverbank, free use of the canoe
Exceptional
(129 reviews)

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

Naples

8% off
AU$1,530
for 7 nights, 1 cottage
AU$219 per night
includes taxes & fees
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
The new kitchen has everything needed to prepare a meal and feed eight.
The newly renovated lakeside deck is the hub of activity Spring, Summer & Fall.
... or work on the kitchen island.
The newly renovated living room overlooks the porch room, deck and lake.
Exceptional
(77 reviews)

Tranquil, Serene Sebago Lakefront House on 2 Wooded Acres - 300ft Waterfront!

Casco

8% off
AU$8,290
for 7 nights, 1 home
AU$1,184 per night
includes taxes & fees
Tranquil, Serene Sebago Lakefront House on 2 Wooded Acres - 300ft Waterfront!
Interior
Terrace/patio
Interior
Exterior
Exceptional
(7 reviews)

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

Naples

8% off
AU$6,994
for 7 nights, 1 home
AU$999 per night
includes taxes & fees
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Exterior
Gas firepit installed May 2026.
Dining Room with cherry table, seating for 8 people. View of back yard & deck.
Swimming area at Trickey Pond. 2 single kayaks and life jackets are provided.
Exceptional
(31 reviews)

Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access

Naples

8% off
AU$4,468
for 7 nights, 1 home
AU$638 per night
includes taxes & fees
Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access
Interior
Private kitchen
Just a walk down to the sandy beach
Living area
Exceptional
(15 reviews)

House at Sunshine- Long Lake, 5 min walk to causeway

Naples

8% off
AU$3,524
for 7 nights, 1 home
AU$503 per night
includes taxes & fees
House at Sunshine- Long Lake, 5 min walk to causeway
Interior
Property grounds
Private kitchen
Interior
Exceptional
(10 reviews)

Peaceful Lakeside Oasis Near City Amenities

Windham

8% off
AU$3,489
for 7 nights, 1 home
AU$498 per night
includes taxes & fees
Peaceful Lakeside Oasis Near City Amenities
Kitchen/breakfast bar
Outdoor dining
Living room
Exterior
Exceptional
(21 reviews)

Spacious country house near lakes and skiing, convenient to downtown Bridgton.

Bridgton

12% off
AU$3,414
for 7 nights, 1 home
AU$488 per night
includes taxes & fees
Spacious country house near lakes and skiing, convenient to downtown Bridgton.
Quiescent town of Bridgton, ME. Only13 minutes drive from Vacationland Retreat.
New in 2024: solar lights to complement the cozy experience our fire pit offers.
Blooming rockery in the back yard.
Closest sandy beach at the nearby Woods Pond with the playground for 2-12 y/o
Exceptional
(33 reviews)

Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago

Denmark

8% off
AU$2,515
for 7 nights, 1 home
AU$359 per night
includes taxes & fees
Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago
Exterior
Private kitchen
Property grounds
Interior
Exceptional
(23 reviews)

Modern Mountain Home- Family Friendly Close to Moose Pond / Pleasant Mountain

Bridgton

11% off
AU$2,943
for 7 nights, 1 home
AU$420 per night
includes taxes & fees
Modern Mountain Home- Family Friendly Close to Moose Pond / Pleasant Mountain
living room
one of our two decks
kitchen table
kitchen
Exceptional
(81 reviews)

☼ Maine Lakefront Getaway ☼

New Gloucester

8% off
AU$2,549
for 7 nights, 1 home
AU$364 per night
includes taxes & fees
☼ Maine Lakefront Getaway ☼
Your private deck and entrance.
Walk around behind the garage to access the apartment.
Private kitchen
Room
Exceptional
(16 reviews)

Private studio nestled in woods outside Portland

Westbrook

13% off
AU$2,156
for 7 nights, 1 apartment
AU$308 per night
includes taxes & fees
Private studio nestled in woods outside Portland

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting adventurous Raymond

Learn about the unique charm of Raymond with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Raymond

Are you looking for attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Raymond has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Point Sebago Golf Resort (4.2 mi / 6.8 km)
  • Seacoast Adventure (3.5 mi / 5.6 km)
  • Lost Valley Ski Resort (18.6 mi / 30 km)
  • Blacksmiths (2.6 mi / 4.3 km)
  • Spring Meadows Golf Course (7 mi / 11.3 km)
  • Riverside Municipal Golf Course (15.2 mi / 24.5 km)

Exploring the natural landscape of Raymond

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Raymond. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Panther Pond (1.9 mi / 3 km)
  • Little Sebago Lake (3.2 mi / 5.1 km)
  • Crescent Lake (4.4 mi / 7.1 km)
  • Sebago Lake (5.1 mi / 8.2 km)
  • Trickey Pond (7.4 mi / 12 km)
  • Thompson Lake (11.8 mi / 18.9 km)

Transport to and around Raymond

The nearest airport is in Auburn, ME (LEW-Auburn - Lewiston Municipal), located 13.6 mi (21.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Portland, ME (PWM-Portland Intl. Jetport), which is 19.2 mi (31 km) away.

Frequently asked questions

What is the best area to stay in Raymond when booking a holiday rental?
When considering a holiday rental in Raymond, Maine, the area around the beautiful Sebago Lake is one of the best choices. This picturesque region offers a great blend of natural beauty and recreational activities, making it a popular spot for visitors. There are numerous properties available here, ranging from charming lakeside cottages to spacious family homes, suiting various needs and preferences.Staying near Sebago Lake allows you to indulge in a variety of outdoor pursuits. One of the top attractions in the area is the Sebago Lake State Park, which boasts stunning hiking trails, swimming spots, and picnic areas, great for enjoying a day in nature. Additionally, the nearby Frye Island, accessible by ferry, offers a great experience with its sandy beaches and walking paths.Another appealing neighbourhood is the bustling village centre, where you can find delightful local shops and eateries. This area provides a vibrant setting and is ideal for immersing yourself in the local culture.
Where are the best areas for renting a beach house in Raymond?
For renting a beach house in Raymond, Maine, the area around Crescent Lake is particularly appealing. This picturesque lake offers a range of properties, many of which have direct access to the water, private docks, and stunning views. Visitors can expect amenities such as spacious decks for outdoor dining, fire pits for evening gatherings, and fully equipped kitchens ideal for preparing meals after a day of water activities.Additionally, the nearby Sebago Lake State Park provides further options, where you can find charming cabins that boast proximity to sandy beaches and hiking trails. These rentals typically include outdoor grills, picnic areas, and access to hiking paths that lead to scenic lookouts over the lake.The town centre of Raymond also features local shops and restaurants, enhancing convenience for travellers.
Where are the best Raymond ski resort rentals?
For renting accommodations near the ski resorts in Raymond, Maine, the area around the Pleasant Mountain ski area is ideal. Located just a short drive away, this region offers various rental options, including cosy cabins and spacious chalets that cater to families and groups. Many of these properties come with amenities such as fireplaces, fully equipped kitchens, and outdoor decks, great for enjoying the winter scenery after a day on the slopes.In the immediate vicinity, the towns of Naples and Bridgton also present additional rental opportunities. Here, visitors can find charming lakeside cottages that provide a tranquil retreat, with some featuring hot tubs and access to private docks along the shores of Long Lake. These properties usually offer a combination of comfort and convenience, with local shops and restaurants within easy reach.For those looking to enjoy both skiing and the beautiful Maine outdoors, the area around Sebago Lake offers hiking trails and winter activities, making it a great base for exploring the winter landscape. Accommodations in this region often include amenities such as laundry facilities and ski storage, ensuring a comfortable stay for winter sports enthusiasts.
What is the most popular type of holiday rental accomodation in Raymond?
In Raymond, holiday houses are the most popular type of holiday rental, with around 296 available throughout the area. These spacious properties are often set in picturesque locations, offering amenities such as fully equipped kitchens, large living areas, and outdoor decks or patios, ideal for enjoying the scenic views of the surrounding lakes and forests. Additionally, there are approximately 192 cottages that provide a charming, rustic experience, typically featuring cosy interiors and easy access to nature. For those seeking a more rustic retreat, around 60 cabins are also available, often located in wooded areas, complete with fireplaces and outdoor fire pits for gatherings under the stars.
Are there any family house rentals in Raymond?
In Raymond, Maine, there are numerous family-friendly rental homes available, with around 106 options to choose from. The area offers a variety of spacious rooms suitable for families, often featuring amenities such as full kitchens, ample living spaces, and outdoor areas where children can play. Many properties also provide comforts like Wi-Fi and air conditioning, ensuring a pleasant stay for all.Situated near the stunning Sebago Lake, visitors can enjoy a wealth of outdoor activities, including swimming, fishing, and hiking. The nearby town centre offers local shops and dining options, making it convenient for families to explore the local culture and cuisine.
Can I rent a holiday home with a pool or hot tub in Raymond?
In Raymond, Maine, there are plenty of holiday homes available for rent that feature pools or hot tubs, with approximately 23 options to choose from. This picturesque area, located near the shores of Sebago Lake, offers a serene retreat for travellers looking to unwind. Many of the rental properties come equipped with private pools, hot tubs, and spacious outdoor decks, ideal for family gatherings or relaxing evenings under the stars.You can expect amenities such as fully equipped kitchens for preparing family meals, comfortable living areas, and often beautiful views of the surrounding nature. Some homes may also include access to nearby beaches or hiking trails, adding to the outdoor experience.
Are there pet-friendly house rentals in Raymond?
In Raymond, Maine, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups seeking a relaxing getaway.The area is known for its stunning natural beauty, with easy access to various outdoor activities. Nearby Sebago Lake offers opportunities for swimming, fishing, and hiking, while the surrounding landscapes are superb for leisurely walks with pets.
Are there any remote work holiday rentals in Raymond?
In Raymond, Maine, there are numerous holiday rentals suitable for remote work, with around 560 options available. Many of these properties come equipped with essential amenities such as reliable Wi-Fi, dedicated workspaces, and comfortable rooms, allowing for a productive environment while enjoying a tranquil getaway.The area is known for its beautiful lakes and scenic landscapes, providing a lovely backdrop for breaks from work. Renting a home near Sebago Lake offers opportunities for outdoor activities, including hiking and fishing, while still being able to maintain a work-life balance. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Raymond?
In Raymond, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and decks or patios that provide outdoor spaces for relaxation and enjoying the scenic views. Onsite parking is also a common feature, making it convenient for travellers with their own vehicles. Additionally, many rentals come equipped with coffee and tea makers for a comfortable start to the day. Given Raymond's picturesque lake location, some properties might offer direct access to the lake, enhancing the overall experience for those looking to enjoy water activities or simply relax by the shore.
When is the best time to visit Raymond for a holiday rental?
The best time to visit Raymond for a holiday rental is during the peak season from June to August, with July being particularly popular. This vibrant summer period invites visitors to enjoy the beautiful lakes, outdoor activities, and the welcoming community atmosphere. With warm temperatures averaging between 20 to 30 degrees Celsius, you can indulge in swimming, kayaking, and hiking, all while soaking in the stunning natural beauty of the area.During these summer months, Raymond buzzes with activity, making it ideal for travellers. You can explore the picturesque Sebago Lake, which offers an array of water sports and picnic spots great for relaxation. The local farmers' markets and community events add to the lively experience, allowing you to engage with locals and sample fresh produce.For those looking for a more budget-friendly option, November presents a quieter and more affordable time to visit. While the weather cools down, averaging around 0 to 10 degrees Celsius, it provides a peaceful escape and an opportunity to enjoy the area's natural beauty without the summer crowds. This month is great for those who appreciate a slower pace and the charm of autumn in New England.
What are the top attractions in Raymond?
In Raymond, Maine, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The stunning Sebago Lake is a major draw, offering opportunities for swimming, boating, and fishing, with several parks and beaches lining the shore. The Raymond Village area has charming shops and local eateries, making it a pleasant spot to explore.For those interested in hiking, the nearby Raymond Community Forest provides well-marked trails that allow for peaceful walks amidst the woods. Additionally, the picturesque views from the summit of Mount Tire'm, which is just a short drive away, are not to be missed, especially during the fall when the foliage is vibrant.The area also hosts various seasonal festivals and events, showcasing local artisans and community spirit.
Are all fees included in the Raymond holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Raymond holiday homes with parking?
Stayz offers a wide selection of holiday homes in Raymond with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Raymond holiday homes?
You can find great discounts on holiday homes in Raymond on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Raymond holiday home booking on Stayz?
To find Raymond holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Raymond?
A long-stay holiday home in Raymond is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Raymond holiday home?
Book your Raymond holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Raymond?
Prices for holiday homes in Raymond vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Raymond to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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