Holiday rentals near Thanksgiving Farm Wines
We found 1,321 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:2 Oct - 9 Oct
Image gallery for Spacious Charming DC Row House + Free parking-Sleeps 17 guests
9.29.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)
Spacious Charming DC Row House + Free parking-Sleeps 17 guests
Washington
7% off
Price is AU$3,528
AU$3,528
for 7 nights, 1 home
AU$504 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$1,395
AU$1,395
for 7 nights, 1 room
AU$199 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, (18 reviews)
Exceptional
(18 reviews)
Captain's Retreat! Newly Renovated - few steps from the beach!
Annapolis
16% off
Price is AU$8,344
AU$8,344
for 7 nights, 1 home
AU$1,192 per night
includes taxes & fees
Image gallery for Waterfront Architectural Masterpiece with private dockage available.
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Waterfront Architectural Masterpiece with private dockage available.
Annapolis
7% off
Price is AU$14,712
AU$14,712
for 7 nights, 1 home
AU$2,102 per night
includes taxes & fees
Image gallery for Waterfront Home near Annapolis, MD
1010 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Waterfront Home near Annapolis, MD
Galesville
8% off
Price is AU$19,496
AU$19,496
for 7 nights, 1 home
AU$2,785 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, (13 reviews)
Exceptional
(13 reviews)
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Annapolis
8% off
Price is AU$6,133
AU$6,133
for 7 nights, 1 home
AU$876 per night
includes taxes & fees
Image gallery for Charming 3BDR Bungalow Near Annapolis
9.69.6 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Charming 3BDR Bungalow Near Annapolis
Riva
9% off
Price is AU$3,292
AU$3,292
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Image gallery for Mins to Annap; Luxury Townhome
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Mins to Annap; Luxury Townhome
Arnold
8% off
Price is AU$7,464
AU$7,464
for 7 nights, 1 home
AU$1,066 per night
includes taxes & fees
Image gallery for Water Views - Close to Downtown Annapolis
1010 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)
Water Views - Close to Downtown Annapolis
Annapolis
5% off
Price is AU$7,156
AU$7,156
for 7 nights, 1 home
AU$1,022 per night
includes taxes & fees
Image gallery for Annapolis Tree House Apartment- luxury shower, separate space
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Annapolis Tree House Apartment- luxury shower, separate space
Annapolis
7% off
Price is AU$2,539
AU$2,539
for 7 nights, 1 apartment
AU$363 per night
includes taxes & fees
Image gallery for Circa 1700 Chesapeake Colonial home on the National Register.
9.89.8 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville
8% off
Price is AU$5,615
AU$5,615
for 7 nights, 1 home
AU$802 per night
includes taxes & fees
Image gallery for Waterfront Sanctuary only 50 Min. From DC/Balt.
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Waterfront Sanctuary only 50 Min. From DC/Balt.
Shady Side
12% off
Price is AU$8,081
AU$8,081
for 7 nights, 1 home
AU$1,154 per night
includes taxes & fees
Image gallery for The General's House-Spacious Home w/Pool & Hot Tub
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
The General's House-Spacious Home w/Pool & Hot Tub
Annapolis
7% off
Price is AU$11,564
AU$11,564
for 7 nights, 1 home
AU$1,652 per night
includes taxes & fees
Image gallery for Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Stevensville
8% off
Price is AU$6,242
AU$6,242
for 7 nights, 1 home
AU$892 per night
includes taxes & fees
Image gallery for Edgewater's Shelby on the Bay
9.49.4 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Edgewater's Shelby on the Bay
Edgewater
7% off
Price is AU$6,564
AU$6,564
for 7 nights, 1 home
AU$938 per night
includes taxes & fees
Image gallery for Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
9.89.8 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Annapolis
8% off
Price is AU$7,274
AU$7,274
for 7 nights, 1 home
AU$1,039 per night
includes taxes & fees
Image gallery for Guest Quarters at the Inn - 102
9.89.8 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Guest Quarters at the Inn - 102
North Beach
8% off
Price is AU$2,123
AU$2,123
for 7 nights, 1 apartment
AU$303 per night
includes taxes & fees
Image gallery for The Liberty House- Pristine Renovation with parking,
1010 out of 10, Exceptional, (53 reviews)
Exceptional
(53 reviews)
The Liberty House- Pristine Renovation with parking,
Annapolis
8% off
Price is AU$6,020
AU$6,020
for 7 nights, 1 home
AU$860 per night
includes taxes & fees
Image gallery for Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Riva
8% off
Price is AU$5,941
AU$5,941
for 7 nights, 1 home
AU$849 per night
includes taxes & fees
Image gallery for Heart of Historic District!
9.89.8 out of 10, Exceptional, (176 reviews)
Exceptional
(176 reviews)
Heart of Historic District!
Annapolis
26% off
Price is AU$4,671
AU$4,671
for 7 nights, 1 home
AU$667 per night
includes taxes & fees
Image gallery for Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
Riva
21% off
Price is AU$4,161
AU$4,161
for 7 nights, 1 home
AU$594 per night
includes taxes & fees
Image gallery for VIBES! Breakfast - Free Parking/Piano/King Bed
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
VIBES! Breakfast - Free Parking/Piano/King Bed
Washington
7% off
Price is AU$1,343
AU$1,343
for 7 nights, 1 home
AU$192 per night
includes taxes & fees
Image gallery for Cozy Cottage with Beach Access
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Cozy Cottage with Beach Access
Annapolis
7% off
Price is AU$4,465
AU$4,465
for 7 nights, 1 home
AU$638 per night
includes taxes & fees
Image gallery for Annapolis waterfront "tiny house" in garden setting
1010 out of 10, Exceptional, (261 reviews)
Exceptional
(261 reviews)
Annapolis waterfront "tiny house" in garden setting
Annapolis
8% off
Price is AU$1,735
AU$1,735
for 7 nights, 1 cottage
AU$248 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
Welcoming Waterfront Luxury Estate for Family, Friends, and Pets in Annapolis
Sleeps 14 · 6 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
Sleeps 12 · 6 bedrooms · 4+ bathrooms
8,000 Sq Ft Luxury Estate Near Annapolis | Sleeps 32 | Pool, Theater & Pickleball
Sleeps 32 · 8 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
Waterfront Escape with Pool Nature Lover Paradise
Sleeps 16 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!
Sleeps 12 · 5 bedrooms · 4 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