Holiday rentals near Thanksgiving Farm Wines
We found 1,369 holiday rentals — enter your dates for availability
Choose the perfect holiday home that's near Thanksgiving Farm Wines. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and a hot tub. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts – Thanksgiving Farm Wines
Showing deals for:1 Jan - 8 Jan
Image gallery for Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Stevensville
12% off
Price is AU$3,155
AU$3,155
for 7 nights, 1 room
AU$451 per night
includes taxes & fees
Image gallery for Luxury 5Brooms 4,5Baths Home &Free parking Near DC
9.69.6 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Luxury 5Brooms 4,5Baths Home &Free parking Near DC
Glenn Dale
8% off
Price is AU$5,884
AU$5,884
for 7 nights, 1 room
AU$841 per night
includes taxes & fees
Image gallery for Modern 1BR Near DC – Quiet Comfort, Fast Commute
9.69.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Modern 1BR Near DC – Quiet Comfort, Fast Commute
District Heights
8% off
Price is AU$1,380
AU$1,380
for 7 nights, 1 room
AU$197 per night
includes taxes & fees
Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!
9.89.8 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Captain's Retreat! Newly Renovated - few steps from the beach!
Annapolis
16% off
Price is AU$5,898
AU$5,898
for 7 nights, 1 home
AU$843 per night
includes taxes & fees
Image gallery for West Annapolis Cottage- 6BR Walk to Navy Stadium
1010 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
West Annapolis Cottage- 6BR Walk to Navy Stadium
Annapolis
7% off
Price is AU$9,536
AU$9,536
for 7 nights, 1 home
AU$1,362 per night
includes taxes & fees
Image gallery for Chesapeake Bay Cottage
1010 out of 10, Exceptional, (94 reviews)
Exceptional
(94 reviews)
Chesapeake Bay Cottage
Churchton
8% off
Price is AU$3,489
AU$3,489
for 7 nights, 1 cottage
AU$498 per night
includes taxes & fees
Image gallery for Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
1010 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Annapolis
8% off
Price is AU$5,421
AU$5,421
for 7 nights, 1 home
AU$774 per night
includes taxes & fees
Image gallery for Waterfront Architectural Masterpiece with private dockage available.
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Waterfront Architectural Masterpiece with private dockage available.
Annapolis
7% off
Price is AU$14,461
AU$14,461
for 7 nights, 1 home
AU$2,066 per night
includes taxes & fees
Image gallery for Waterfront Home near Annapolis, MD
1010 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
Waterfront Home near Annapolis, MD
Galesville
8% off
Price is AU$19,152
AU$19,152
for 7 nights, 1 home
AU$2,736 per night
includes taxes & fees
Image gallery for Charming Home located minutes from the Naval Academy and Downtown Annapolis
9.69.6 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Annapolis
8% off
Price is AU$6,022
AU$6,022
for 7 nights, 1 home
AU$860 per night
includes taxes & fees
Image gallery for Charming Annapolis WaterVIEW Home
9.89.8 out of 10, Exceptional, (78 reviews)
Exceptional
(78 reviews)
Charming Annapolis WaterVIEW Home
Annapolis
12% off
Price is AU$4,540
AU$4,540
for 7 nights, 1 home
AU$649 per night
includes taxes & fees
Image gallery for Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
9.89.8 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Annapolis
12% off
Price is AU$8,706
AU$8,706
for 7 nights, 1 home
AU$1,244 per night
includes taxes & fees
Image gallery for Annapolis Tree House Apartment- luxury shower, separate space
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Annapolis Tree House Apartment- luxury shower, separate space
Annapolis
7% off
Price is AU$2,500
AU$2,500
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
Image gallery for Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
1010 out of 10, Exceptional, (164 reviews)
Exceptional
(164 reviews)
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Sherwood
10% off
Price is AU$3,202
AU$3,202
for 7 nights, 1 home
AU$457 per night
includes taxes & fees
Image gallery for Million Dollar View of the Chesapeake Bay
9.89.8 out of 10, Exceptional, (141 reviews)
Exceptional
(141 reviews)
Million Dollar View of the Chesapeake Bay
Deale
8% off
Price is AU$3,696
AU$3,696
for 7 nights, 1 home
AU$528 per night
includes taxes & fees
Image gallery for 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
1010 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
8% off
Price is AU$10,112
AU$10,112
for 7 nights, 1 home
AU$1,445 per night
includes taxes & fees
Image gallery for River Terrace Retreat: Free Parking and Garden Views
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
River Terrace Retreat: Free Parking and Garden Views
Washington
7% off
Price is AU$3,196
AU$3,196
for 7 nights, 1 home
AU$457 per night
includes taxes & fees
Image gallery for Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
1010 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Stevensville
8% off
Price is AU$9,330
AU$9,330
for 7 nights, 1 home
AU$1,333 per night
includes taxes & fees
Image gallery for Charming 3BDR Bungalow Near Annapolis
9.89.8 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Charming 3BDR Bungalow Near Annapolis
Riva
9% off
Price is AU$3,233
AU$3,233
for 7 nights, 1 home
AU$462 per night
includes taxes & fees
Image gallery for Circa 1700 Chesapeake Colonial home on the National Register.
9.89.8 out of 10, Exceptional, (66 reviews)
Exceptional
(66 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville
8% off
Price is AU$4,658
AU$4,658
for 7 nights, 1 home
AU$665 per night
includes taxes & fees
Image gallery for Fabulous 5-bedroom house with AC in charming Annapolis
8.88.8 out of 10, Excellent, (12 reviews)
Excellent
(12 reviews)
Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8% off
Price is AU$5,110
AU$5,110
for 7 nights, 1 home
AU$730 per night
includes taxes & fees
Image gallery for Annapolis waterfront "tiny house" in garden setting
1010 out of 10, Exceptional, (270 reviews)
Exceptional
(270 reviews)
Annapolis waterfront "tiny house" in garden setting
Annapolis
8% off
Price is AU$1,689
AU$1,689
for 7 nights, 1 cottage
AU$241 per night
includes taxes & fees
Image gallery for Unbelievable beach views for 6
9.49.4 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Unbelievable beach views for 6
North Beach
8% off
Price is AU$3,013
AU$3,013
for 7 nights, 1 apartment
AU$430 per night
includes taxes & fees
Image gallery for Private Resort! 100" Home Theater, HotTub, Pool, Basketball Court, extra games
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Private Resort! 100" Home Theater, HotTub, Pool, Basketball Court, extra games
Bowie
8% off
Price is AU$8,392
AU$8,392
for 7 nights, 1 home
AU$1,199 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Thanksgiving Farm Wines
Kent Island Waterfront Retreat
Sleeps 16 · 5 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
LUXE Private Waterfront Retreat with Pool, Hot Tub and Game Room for Family Fun
Sleeps 14 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
42 reviews(42 reviews)
Pool & Yard Retreat | 4BR | 20 Min to Annapolis
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.09.0 out of 10
Wonderfulwonderful
9 reviews(9 reviews)
Coastal Edgewater Home w/ Private Hot Tub!
Sleeps 9 · 5 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
21 reviews(21 reviews)
Million Dollar View of the Chesapeake Bay
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
141 reviews(141 reviews)
8,000 Sq Ft Luxury Estate Near Annapolis | Sleeps 32 | Pool, Theater & Pickleball
Sleeps 32 · 8 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value