Location

Dates

Guests

Vacation rentals in Middletown, Connecticut, United States

Comfortable 3BR Home Near Yale & Quinnipiac

Comfortable 3BR Home Near Yale & Quinnipiac

Comfortable 3BR Home Near Yale & Quinnipiac

Comfortable 3BR Home Near Yale & Quinnipiac

Comfortable 3BR Home Near Yale & Quinnipiac

Comfortable 3BR Home Near Yale & Quinnipiac

3 bedrooms·1 bath

North Haven • Connecticut

973,51 $ USD totalt för 3 nätter

1–4 okt. 2026

Charming cottage with covered porch, large fenced yard, and parking.

Bright, modern bath with marble-tile shower and sleek storage vanity

Cozy kitchenette with breakfast bar and sunny dining nook

Cozy kitchen with breakfast bar, wood counters & open layout

Cozy suite with kitchenette, wall-mounted TV, and adjoining bath.

10C Front

3 bedrooms·2 baths

Windsor • Connecticut

597,00 $ USD totalt för 3 nätter

31 dec. 2026–3 jan. 2027

#32- Sleeps 10! Litchfield County

#32- Sleeps 10! Litchfield County

#32- Sleeps 10! Litchfield County

#32- Sleeps 10! Litchfield County

#32- Sleeps 10! Litchfield County

#32- Sleeps 10! Litchfield County

3 bedrooms·2 baths

Plymouth • Connecticut

1 099,20 $ USD totalt för 4 nätter

4–8 okt. 2026

Spacious 1 Bed Apt - Litchfield County

Spacious 1 Bed Apt - Litchfield County

Spacious 1 Bed Apt - Litchfield County

Spacious 1 Bed Apt - Litchfield County

Spacious 1 Bed Apt - Litchfield County

Spacious 1 Bed Apt - Litchfield County

1 bedroom·1 bath

Plymouth • Connecticut

1 195,20 $ USD totalt för 7 nätter

1–8 okt. 2026

#33- Newly Constructed - Luxury Collection

#33- Newly Constructed - Luxury Collection

#33- Newly Constructed - Luxury Collection

#33- Newly Constructed - Luxury Collection

#33- Newly Constructed - Luxury Collection

#33- Newly Constructed - Luxury Collection

0 bedrooms·1 bath

Plymouth • Connecticut

925,20 $ USD totalt för 4 nätter

2–6 okt. 2026

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 totalt för 3 nätter

4–7 okt. 2026

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

1 082,50 $ USD totalt för 3 nätter

4–7 okt. 2026

Quiet & Cozy Room by SCSU and Yale

Quiet & Cozy Room by SCSU and Yale

Quiet & Cozy Room by SCSU and Yale

Quiet & Cozy Room by SCSU and Yale

Quiet & Cozy Room by SCSU and Yale

Quiet & Cozy Room by SCSU and Yale

1 bedroom·1 bath

New Haven • Connecticut

970,34 $ USD totalt för 14 nätter

11–25 okt. 2026

Communal lounge

Communal lounge

Spacious 2BR Suite Near Yale & SCSU

2 bedrooms·1 bath

New Haven • Connecticut

900,00 $ USD totalt för 6 nätter

1–7 okt. 2026

Private Room near Yale & Yale Hospital

Private Room near Yale & Yale Hospital

Private Room near Yale & Yale Hospital

Private Room near Yale & Yale Hospital

Private Room near Yale & Yale Hospital

Private Room near Yale & Yale Hospital

1 bedroom·1 bath

New Haven • Connecticut

327,43 $ USD totalt för 5 nätter

16–21 dec. 2026

Cozy Bedroom next to SCSU and Yale

Cozy Bedroom next to SCSU and Yale

Cozy Bedroom next to SCSU and Yale

Cozy Bedroom next to SCSU and Yale

Cozy Bedroom next to SCSU and Yale

Cozy Bedroom next to SCSU and Yale

1 bedroom·1 bath

New Haven • Connecticut

431,40 $ USD totalt för 5 nätter

1–6 okt. 2026

Restful nights await in this bedroom adorned with a queen-size bed. The sophisticated decor and thoughtfully chosen furnishings create an elegant haven for peaceful slumber.

Living room with beautiful white sofa, and green chair

Beautiful Gazebo tent with a 10 seater outdoor dining table set, Coca-Cola cooler, Grill and a sitting area around a fire-pit

Beautiful dedicated work space with a lamp

Haven 4 mins from Yale | Fire Pit | Outdoor dining

4 bedrooms·2 baths

New Haven • Connecticut

4.8(30 reviews)

1 202,00 $ USD totalt för 3 nätter

1–4 okt. 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 totalt för 3 nätter

5–8 okt. 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/ natt(exkl. avgifter & skatter)

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/ natt(exkl. avgifter & skatter)

Experience breathtaking sunsets just steps away! Take a leisurely stroll and witness nature's stunning masterpiece as the sky ignites with vibrant hues.

Great Hammcock Getaway, Walk to the beach, Hot tub

Gather around our outdoor gas fire pit for cozy evenings under the stars! Perfect for sharing stories, or simply enjoying the warmth of the flames. Our fire pit provides the ideal setting for memorable moments with loved ones.

Dine al fresco in style with our outdoor dining table and chairs! Whether you're enjoying a meal with family or hosting a barbecue with friends, our spacious setup provides the perfect backdrop for memorable gatherings under the open sky.

Dive into relaxation in our 4-person hot tub! Perfect for couples or friends, soak under the stars and melt your stress away in bubbling warmth.

Great Hammcock Getaway, Walk to the beach, Hot tub

3 bedrooms·1½ baths

Old Saybrook • Connecticut

5(17 reviews)

1 185,00 $ USD totalt för 3 nätter

1–4 okt. 2026

3BR Home Near Yale & Tweed Airport

3BR Home Near Yale & Tweed Airport

3 bedrooms·2 baths

New Haven • Connecticut

$130 – $282/ natt(exkl. avgifter & skatter)

Welcome to your private beach retreat!

Fully Stocked Kitchen

Downstairs Bedroom

Living / Dining Room

Sky of Blue, Sea of Green

4 bedrooms·2 baths

Old Lyme • Connecticut

1 129,75 $ USD totalt för 3 nätter

1–4 okt. 2026

#34- Stunning-Newly Remodeled

#34- Stunning-Newly Remodeled

#34- Stunning-Newly Remodeled

#34- Stunning-Newly Remodeled

#34- Stunning-Newly Remodeled

#34- Stunning-Newly Remodeled

2 bedrooms·1 bath

Old Lyme • Connecticut

1 831,20 $ USD totalt för 7 nätter

1–8 okt. 2026

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven

3 bedrooms·1 bath

Old Lyme • Connecticut

2 317,20 $ USD totalt för 7 nätter

1–8 okt. 2026