A valley with autumn foliage, a river, and distant hills.

Prospect Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Prospect vacation rentals

Interior

1. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is AED 404
AED 538 total
includes taxes & fees
27 Sep - 28 Sep
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Exterior detail

2. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is AED 430
AED 1,159 total
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
Smart TV

3. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.0 out of 10, Wonderful, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is AED 443
AED 752 total
includes taxes & fees
29 Sep - 30 Sep
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
TV

4. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is AED 1,006
AED 1,925 total
includes taxes & fees
6 Oct - 7 Oct
#43- Modern Luxury Log Cabin Retreat - Fire Pit
Exterior detail

5. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is AED 551
AED 1,383 total
includes taxes & fees
1 Oct - 2 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
1 bedroom, iron/ironing board, WiFi, bed sheets

6. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
The price is AED 433
AED 1,031 total
includes taxes & fees
27 Sep - 28 Sep
Once the old Schools house now a newly furnished Apartment
Coffee/tea maker, fridge, microwave, oven

7. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
The price is AED 433
AED 1,031 total
includes taxes & fees
27 Sep - 28 Sep
All New Fully Furnished Cozy Studio
Interior

8. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
The price is AED 274
AED 389 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Studio apartment in delightful Waterbury with Central Air
Exterior

9. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is AED 324
AED 446 total
includes taxes & fees
27 Sep - 28 Sep
Cozy One Bedroom Apartment Centrally Located in Southbury
Smart TV

10. #23 COMFORT & LUXURY 3 BR/2 BA House

#23 COMFORT & LUXURY 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is AED 602
AED 1,262 total
includes taxes & fees
27 Sep - 28 Sep
#23 COMFORT & LUXURY 3 BR/2 BA House
House (3 Bedrooms) | Interior

11. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is AED 1,003
AED 1,980 total
includes taxes & fees
27 Sep - 28 Sep
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
TV, fireplace

12. #30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is AED 695
AED 1,626 total
includes taxes & fees
27 Sep - 28 Sep
#30 - Spacious & Cozy!
TV

13. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is AED 433
AED 1,031 total
includes taxes & fees
5 Oct - 6 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
Exterior

14. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is AED 433
AED 1,031 total
includes taxes & fees
29 Sep - 30 Sep
All New Studio apartment in center of town
Iron/ironing board, WiFi, bed sheets

15. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is AED 992
AED 2,223 total
includes taxes & fees
27 Sep - 28 Sep
The Cottage by the Woods -private getaway to relax
Interior

16. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AED 349
AED 475 total
includes taxes & fees
26 Oct - 27 Oct
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Coffee/tea maker, fridge, microwave, oven

17. Renovated 2 bedroom entire apartment w/parking

Renovated 2 bedroom entire apartment w/parking
Ansonia
10.0 out of 10, Exceptional, (2 reviews)
"Host was very attentive making sure everything was going well, apartment was great would definitely stay again "
United States
Sophia
The price is AED 521
AED 906 total
includes taxes & fees
27 Sep - 28 Sep
Renovated 2 bedroom entire apartment w/parking
Coffee/tea maker, fridge, microwave, oven

18. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is AED 500
AED 1,007 total
includes taxes & fees
1 Oct - 2 Oct
Private Apartment in Southbury 103
Interior

19. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is AED 804
AED 1,873 total
includes taxes & fees
27 Sep - 28 Sep
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Coffee/tea maker, fridge, microwave, oven

20. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is AED 804
AED 1,663 total
includes taxes & fees
5 Oct - 6 Oct
#27- Luxury Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Prospect Hotel Reviews

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"Clean and convenient location. Helpful staff."
James 1-night trip
Posted 1 day ago
Hotel Marcel New Haven, Tapestry Collection By Hilton
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

10/10 Excellent
"Great experience again enjoy the location and quiet"
Herbert 2-night trip
Posted 2 days ago
Motel 6 New Haven - Branford, CT

Frequently asked questions

Can I find a vacation rental in Prospect?

Yes, we have vacation rentals close to top sights in Prospect, or you can go with a more remote option if you'd like a relaxing place to stay. Prospect is known for its golf courses and bars.

What are some of the best vacation home rentals in Prospect?

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy: Visitors like this Prospect vacation home rental. It is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Prospect?

While exploring the area, visit family-friendly sights like Cheshire Hollow Farm, or get outside and enjoy nature at Waterbury Green. In the larger area, you’ll find Palace Theatre and Waterbury City Hall.

What’s a vacation rental in Prospect like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Prospect. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.