Location

Dates

Guests

Vacation rentals in Prospect, Connecticut, United States

#22- 4B/2Ba- Central CT

#22- 4B/2Ba- Central CT

#22- 4B/2Ba- Central CT

#22- 4B/2Ba- Central CT

#22- 4B/2Ba- Central CT

#22- 4B/2Ba- Central CT

4 bedrooms·2 baths

New Britain • Connecticut

$1,375.20 USD total for 4 nights

Oct 26 – 30, 2026

#42 - Stunning Modern 2 Br Home - 2 Min From Hwy

#42 - Stunning Modern 2 Br Home - 2 Min From Hwy

#42 - Stunning Modern 2 Br Home - 2 Min From Hwy

#42 - Stunning Modern 2 Br Home - 2 Min From Hwy

#42 - Stunning Modern 2 Br Home - 2 Min From Hwy

#42 - Stunning Modern 2 Br Home - 2 Min From Hwy

2 bedrooms·1 bath

Berlin • Connecticut

$656.40 USD total for 3 nights

Oct 25 – 28, 2026

#40 - Spacious, Sleek & Cozy *Sleeps 10*

#40 - Spacious, Sleek & Cozy *Sleeps 10*

#40 - Spacious, Sleek & Cozy *Sleeps 10*

#40 - Spacious, Sleek & Cozy *Sleeps 10*

#40 - Spacious, Sleek & Cozy *Sleeps 10*

#40 - Spacious, Sleek & Cozy Sleeps 10

3 bedrooms·2 baths

Middletown • Connecticut

$890.40 USD total for 3 nights

Oct 12 – 15, 2026

#28- *Modern Bungalow*

#28- *Modern Bungalow*

#28- *Modern Bungalow*

#28- *Modern Bungalow*

#28- *Modern Bungalow*

#28- Modern Bungalow

2 bedrooms·1 bath

New Britain • Connecticut

$7,284.00 USD total for 30 nights

Nov 6 – Dec 6, 2026

3BR Home Near Yale & Tweed Airport

3BR Home Near Yale & Tweed Airport

3 bedrooms·2 baths

New Haven • Connecticut

$130 – $282/ night(excl. fees & taxes)

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat

2 bedrooms·1 bath

Middletown • Connecticut

$1,081.20 USD total for 4 nights

Oct 21 – 25, 2026

#37 - Luxury Collection

#37 - Luxury Collection

#37 - Luxury Collection

#37 - Luxury Collection

#37 - Luxury Collection

#37 - Luxury Collection

2 bedrooms·2 baths

Stratford • Connecticut

$890.40 USD total for 3 nights

Oct 1 – 4, 2026

Coastal Modern Retreat: Beach Access & Water Views

Bright minimalist dresser with stylish decor and warm hardwood floors

Sunny patio with a spacious gas grill for easy outdoor cookouts

Bright, serene bedroom with mirrored closets and stylish woven headboard

Bright, spotless bathroom with marble-look tile and fresh guest touches

Coastal Modern Retreat: Beach Access & Water Views

7 bedrooms·5 baths

Branford • Connecticut

$2,395.50 USD total for 3 nights

Oct 5 – 8, 2026

Coastal Modern Retreat: Beach Access & Water Views

Coastal Modern Retreat: Beach Access & Water Views

Coastal Modern Retreat: Beach Access & Water Views

Coastal Modern Retreat: Beach Access & Water Views

Coastal Modern Retreat: Beach Access & Water Views

Coastal Modern Retreat: Beach Access & Water Views

7 bedrooms·5 baths

Branford • Connecticut

$670 – $1,422/ night(excl. fees & taxes)

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath

5 bedrooms·2 baths

Middletown • Connecticut

$1,500.00 USD total for 3 nights

Oct 1 – 4, 2026

The Dream Location for Your Perfect Vacation

Welcome to Sunset Beach

Newly updated exterior.

The Dream Location for Your Perfect Vacation

Private Entrance

The Dream Location for Your Perfect Vacation

3 bedrooms·1 bath

Branford • Connecticut

4.98(43 reviews)

$300/ night(excl. fees & taxes)

90-Sec Walk to Beach | Walnut Beach Luxury House image 2

Open-plan living, dining, and kitchen area

Chef’s kitchen with quartz island

Poker nights, chess, board games, putting competitions, or simply gathering together long after dinner ends.

King Suite Bathed in luxurious linens and light.

Walnut Beach Luxury House | 90-Sec Walk to Beach

3 bedrooms·2 baths

Milford • Connecticut

5(9 reviews)

$2,620.00 USD total for 3 nights

Oct 4 – 7, 2026

Coastal Milford Retreat

Coastal Milford Retreat

Coastal Milford Retreat

Coastal Milford Retreat

Coastal Milford Retreat

Coastal Milford Retreat

3 bedrooms·1 bath

Milford • Connecticut

5(25 reviews)

$2,270.00 USD total for 4 nights

Oct 1 – 5, 2026

Private Room / Near Yale Bridgeport / 30+ Day Stay

Private Room / Near Yale Bridgeport / 30+ Day Stay

Private Room / Near Yale Bridgeport / 30+ Day Stay

Private Room / Near Yale Bridgeport / 30+ Day Stay

Private Room / Near Yale Bridgeport / 30+ Day Stay

Private Room / Near Yale Bridgeport / 30+ Day Stay

1 bedroom·1 bath

Bridgeport • Connecticut

$985.20 USD total for 14 nights

Oct 1 – 15, 2026

Private Room I Near Yale Bridgeport I 30 Day Stay

Private Room I Near Yale Bridgeport I 30 Day Stay

Private Room I Near Yale Bridgeport I 30 Day Stay

Private Room I Near Yale Bridgeport I 30 Day Stay

Private Room I Near Yale Bridgeport I 30 Day Stay

Private Room I Near Yale Bridgeport I 30 Day Stay

1 bedroom·1 bath

Bridgeport • Connecticut

$429.01 USD total for 5 nights

Dec 29, 2026 – Jan 3, 2027

Cozy Yale Haven | Modern & Steps Away

Cozy Yale Haven | Modern & Steps Away

Cozy Yale Haven | Modern & Steps Away

Cozy Yale Haven | Modern & Steps Away

1 bedroom·1 bath

Bridgeport • Connecticut

$1,121.70 USD total for 14 nights

Oct 29 – Nov 12, 2026

Medical Professional | Room Near Hospital

Medical Professional | Room Near Hospital

Medical Professional | Room Near Hospital

Medical Professional | Room Near Hospital

1 bedroom·1 bath

Bridgeport • Connecticut

$960.42 USD total for 14 nights

Oct 30 – Nov 13, 2026

Furnished Room for Travel Nurses | 30+ Day Stay

Furnished Room for Travel Nurses | 30+ Day Stay

Furnished Room for Travel Nurses | 30+ Day Stay

Furnished Room for Travel Nurses | 30+ Day Stay

1 bedroom·1 bath

Bridgeport • Connecticut

$1,002.00 USD total for 14 nights

Nov 10 – 24, 2026

Spacious Family Home, Sleeps 10, Pet-Friendly

Spacious Family Home, Sleeps 10, Pet-Friendly

Spacious Family Home, Sleeps 10, Pet-Friendly

Spacious Family Home, Sleeps 10, Pet-Friendly

Spacious Family Home, Sleeps 10, Pet-Friendly

Spacious Family Home, Sleeps 10, Pet-Friendly

4 bedrooms·2 baths

Bridgeport • Connecticut

$1,246.62 USD total for 3 nights

Oct 4 – 7, 2026

Quintessential Brooklawn

Quintessential Brooklawn

Quintessential Brooklawn

Quintessential Brooklawn

Quintessential Brooklawn

Quintessential Brooklawn

4 bedrooms·2 baths

Bridgeport • Connecticut

5(4 reviews)

$1,355.05 USD total for 3 nights

Oct 4 – 7, 2026

View from upper deck

View from Spellman Point Road toward the lake. Game building (former garage) on the left. Ping pong, full size pool table, and EV charger in here!

Large sunny deck with plenty of seating

Upper patio. The game building (former garage) is on the left, the main entry to the house is to the left of the bench and table.

The kids (and adults!) will love sliding into the water on this floating slide.

Fun on the Lake

4 bedrooms·3 baths

East Hampton • Connecticut

5(18 reviews)

$2,556.45 USD total for 3 nights

Oct 4 – 7, 2026

Bright, modern half-bath with window, sleek vanity, and black tile floor.

Bright modern kitchen with stainless appliances and stone countertops.

Charming ranch with red door, lush landscaping, and stone walkway

Bright open-plan living with modern kitchen, hardwoods, and garden view

Bright flex room with wood-look floors and recessed lighting

100P Retreat

3 bedrooms·1½ baths

Glastonbury • Connecticut

$561.00 USD total for 3 nights

Dec 31, 2026 – Jan 3, 2027

Gilean:"The bed is comfortable. The room has a microwave and a small refrigerator. It is a nice, well kept up home in a safe neighborhood."

Susan:"...bathroom was spacious and clean."

The live-in dogs. They are allowed in all common areas.
Corrina:"Their dogs are loving and adorable"

Laurie: "Queenie and Ted are warm and welcoming and made me feel completely at home. "

The kitchen - feel free to cook for yourself!

Queen Room with Private Bath

1 bedroom·1½ baths

Glastonbury • Connecticut

5(67 reviews)

$75/ night(excl. fees & taxes)

Historic Coastal Home • Marsh Views • Pet-Friendly

Historic Coastal Home • Marsh Views • Pet-Friendly

Historic Coastal Home • Marsh Views • Pet-Friendly

Historic Coastal Home • Marsh Views • Pet-Friendly

Historic Coastal Home • Marsh Views • Pet-Friendly

Historic Coastal Home • Marsh Views • Pet-Friendly

4 bedrooms·3½ baths

Clinton • Connecticut

$1,224.64 USD total for 3 nights

Oct 4 – 7, 2026